2-[(Anilino)(2-nitro­phen­yl)meth­yl]cyclo­hexa­none

Eftekhari-Sis, B.; Mohajer, S.; Büyükgüngör, O.

doi:10.1107/S1600536812036859

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2829

https://doi.org/10.1107/S1600536812036859

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2-[(Anilino)(2-nitrophenyl)methyl]cyclohexanone

Bagher Eftekhari-Sis,^a ^* Sahar Mohajer ^a and Orhan Büyükgüngör ^b

^aDepartment of Chemistry, University of Maragheh, Maragheh, Iran, and ^bDepartment of Physics, Ondokuz Mayis University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: eftekharisis@maragheh.ac.ir

(Received 17 August 2012; accepted 26 August 2012; online 1 September 2012)

In the title compound, C₁₉H₂₀N₂O₃, the cyclohexanone ring adopts a chair conformation with the aminomethyl group is positioned equatorially. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by N—H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a ,b ). For the biological activity of β-amino ketones, see: Arend et al. (1998 ). For the anti-inflammatory and antimicrobial activity of β-amino ketones, see: Jadhav et al. (2008 ) and Kalluraya et al. (2001 ), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006 ); Samet et al. (2009 ); Azizi et al. (2006 ); Cordova (2004 ). For related structures, see: Eftekhari-Sis et al. (2012b); Yuan et al. (2007 ); Fun et al. (2009 ).

Experimental

Crystal data

C₁₉H₂₀N₂O₃
M_r = 324.37
Monoclinic, P 2₁ /c
a = 9.0535 (8) Å
b = 11.9947 (7) Å
c = 17.2267 (15) Å
β = 117.355 (6)°
V = 1661.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.62 × 0.43 × 0.21 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.784, T_max = 0.958
10888 measured reflections
3434 independent reflections
2210 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.160
S = 0.97
3434 reflections
221 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.85 (2)	2.31 (2)	2.906 (3)	127.0 (18)
N1—H1A⋯O2ⁱ	0.85 (2)	2.48 (2)	3.246 (3)	150.2 (19)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812036859/fj2593sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036859/fj2593Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812036859/fj2593Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536812036859/fj2593Isup4.cml

checkCIF report

Comment top

β-amino ketones are widely found in natural and un-natural products, which exhibit anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. Mannich reaction (Eftekhari-Sis et al., 2006; Samet et al., 2009; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in synthesis of β-Amino ketones. We have synthesized the title compound and report its structure here, Fig 1. The cyclohexanone ring adopts chair conformation, and aminomethyl moiety is positioned equatorially on ring at C1.

Related literature top

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a,b). For the biological activity of β-amino ketones, see: Arend et al. (1998). For the anti-inflammatory and antimicrobial activity of β-amino ketones, see: Jadhav et al. (2008) and Kalluraya et al. (2001), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006); Samet et al. (2009); Azizi et al. (2006); Cordova (2004). For related structures, see: Eftekhari-Sis et al. (2012b); Yuan et al. (2007); Fun et al. (2009).

Experimental top

The title compound was obtained by adding of 0.04 g of Laponite-HMPC nano composite (Eftekhari-Sis et al., 2012a,b) to a mixture of 0.5 mmol of 2-nitrobenzaldehyde, 0.5 mmol of aniline and 3 equiv. of cyclohexanone and stirring at room temperature for 24 h. After completion of the reaction, 5 ml EtOH was added and catalyst was removed by filtration, and filtrate was concentrated under reduced pressure. The obtained crud product was recrystallized from EtOH to afford title compound in 62% yield. Colorless crystals suitable for crystal structure determination were grown from EtOH.

Structure description top

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a,b). For the biological activity of β-amino ketones, see: Arend et al. (1998). For the anti-inflammatory and antimicrobial activity of β-amino ketones, see: Jadhav et al. (2008) and Kalluraya et al. (2001), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006); Samet et al. (2009); Azizi et al. (2006); Cordova (2004). For related structures, see: Eftekhari-Sis et al. (2012b); Yuan et al. (2007); Fun et al. (2009).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The structure of title compound, showing 35% probability displacement ellipsoids and the atom numbering scheme. Intramolecular hydrogen bond are shown as dashed lines.
	Fig. 2. The stabilization of molecules in the crystal by inter- and intramolecular N—H···O hydrogen bonds and C—H···O interactions.

2-[(Anilino)(2-nitrophenyl)methyl]cyclohexanone top

Crystal data top

C₁₉H₂₀N₂O₃	F(000) = 688
M_r = 324.37	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10888 reflections
a = 9.0535 (8) Å	θ = 1.7–28.1°
b = 11.9947 (7) Å	µ = 0.09 mm⁻¹
c = 17.2267 (15) Å	T = 296 K
β = 117.355 (6)°	Prism, colorless
V = 1661.5 (2) Å³	0.62 × 0.43 × 0.21 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	3434 independent reflections
Radiation source: fine-focus sealed tube	2210 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
rotation method scans	θ_max = 26.5°, θ_min = 2.5°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −11→11
T_min = 0.784, T_max = 0.958	k = −15→14
10888 measured reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.099P)²] where P = (F_o² + 2F_c²)/3
3434 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.79 e Å⁻³
16 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₂₀N₂O₃	V = 1661.5 (2) Å³
M_r = 324.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0535 (8) Å	µ = 0.09 mm⁻¹
b = 11.9947 (7) Å	T = 296 K
c = 17.2267 (15) Å	0.62 × 0.43 × 0.21 mm
β = 117.355 (6)°

Data collection top

Stoe IPDS 2 diffractometer	3434 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2210 reflections with I > 2σ(I)
T_min = 0.784, T_max = 0.958	R_int = 0.043
10888 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	16 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.79 e Å⁻³
3434 reflections	Δρ_min = −0.23 e Å⁻³
221 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3530 (2)	0.26145 (18)	0.22061 (12)	0.0453 (5)
H1	0.2966	0.3031	0.2482	0.054*
C2	0.2739 (2)	0.1473 (2)	0.19939 (13)	0.0505 (5)
C3	0.0911 (3)	0.1470 (3)	0.13652 (16)	0.0690 (7)
H3A	0.0301	0.1828	0.1635	0.083*
H3B	0.0522	0.0707	0.1229	0.083*
C4	0.0580 (3)	0.2080 (3)	0.05272 (15)	0.0731 (8)
H4A	0.1080	0.1670	0.0223	0.088*
H4B	−0.0610	0.2115	0.0149	0.088*
C5	0.1274 (3)	0.3236 (3)	0.07141 (16)	0.0730 (8)
H5A	0.0699	0.3667	0.0969	0.088*
H5B	0.1089	0.3592	0.0172	0.088*
C6	0.3130 (3)	0.3223 (2)	0.13399 (16)	0.0660 (7)
H6A	0.3532	0.3984	0.1468	0.079*
H6B	0.3713	0.2856	0.1059	0.079*
C7	0.5407 (2)	0.26636 (18)	0.28430 (12)	0.0429 (5)
H7	0.5759	0.3436	0.2840	0.052*
C8	0.5807 (2)	0.23927 (17)	0.37935 (12)	0.0414 (4)
C9	0.5888 (2)	0.31751 (17)	0.44110 (13)	0.0448 (5)
C10	0.6289 (3)	0.2903 (2)	0.52741 (15)	0.0574 (6)
H10	0.6344	0.3455	0.5666	0.069*
C11	0.6599 (3)	0.1815 (2)	0.55354 (16)	0.0655 (7)
H11	0.6837	0.1613	0.6102	0.079*
C12	0.6555 (3)	0.1022 (2)	0.49480 (16)	0.0636 (6)
H12	0.6772	0.0281	0.5123	0.076*
C13	0.6193 (3)	0.13097 (19)	0.41035 (14)	0.0531 (5)
H13	0.6209	0.0757	0.3729	0.064*
C14	0.8043 (2)	0.20265 (19)	0.28812 (12)	0.0455 (5)
C15	0.8911 (3)	0.3024 (2)	0.31590 (16)	0.0613 (6)
H15	0.8341	0.3686	0.3111	0.074*
C16	1.0631 (3)	0.3029 (3)	0.35075 (17)	0.0752 (8)
H16	1.1208	0.3698	0.3693	0.090*
C17	1.1495 (3)	0.2056 (3)	0.35827 (16)	0.0750 (9)
H17	1.2650	0.2063	0.3830	0.090*
C18	1.0634 (3)	0.1077 (3)	0.32882 (17)	0.0726 (8)
H18	1.1208	0.0422	0.3320	0.087*
C19	0.8934 (3)	0.1054 (2)	0.29467 (15)	0.0580 (6)
H19	0.8370	0.0381	0.2757	0.070*
N1	0.6308 (2)	0.19843 (17)	0.25075 (11)	0.0467 (4)
N2	0.5569 (2)	0.43539 (16)	0.41868 (13)	0.0545 (5)
O1	0.3490 (2)	0.06234 (15)	0.22935 (12)	0.0718 (5)
O2	0.4393 (2)	0.46052 (15)	0.34977 (12)	0.0711 (5)
O3	0.6465 (3)	0.50448 (17)	0.47103 (14)	0.0861 (6)
H1A	0.593 (3)	0.133 (2)	0.2363 (14)	0.046 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0372 (9)	0.0539 (13)	0.0416 (10)	0.0030 (8)	0.0155 (8)	0.0015 (9)
C2	0.0409 (10)	0.0643 (13)	0.0424 (11)	−0.0054 (8)	0.0158 (8)	0.0008 (9)
C3	0.0425 (11)	0.090 (2)	0.0587 (14)	−0.0105 (11)	0.0094 (10)	0.0033 (13)
C4	0.0445 (12)	0.115 (3)	0.0449 (12)	0.0038 (13)	0.0080 (10)	−0.0011 (13)
C5	0.0605 (14)	0.093 (2)	0.0534 (14)	0.0169 (13)	0.0157 (11)	0.0192 (13)
C6	0.0604 (13)	0.0680 (17)	0.0568 (14)	0.0042 (11)	0.0160 (11)	0.0186 (12)
C7	0.0384 (9)	0.0447 (11)	0.0438 (10)	−0.0013 (8)	0.0173 (8)	−0.0015 (9)
C8	0.0294 (8)	0.0471 (12)	0.0420 (10)	−0.0005 (7)	0.0116 (7)	−0.0023 (9)
C9	0.0356 (9)	0.0486 (12)	0.0474 (11)	0.0007 (8)	0.0166 (8)	−0.0039 (9)
C10	0.0526 (12)	0.0719 (17)	0.0474 (12)	0.0040 (10)	0.0226 (10)	−0.0071 (11)
C11	0.0619 (13)	0.086 (2)	0.0441 (11)	0.0112 (12)	0.0205 (10)	0.0105 (12)
C12	0.0692 (14)	0.0574 (16)	0.0569 (14)	0.0108 (11)	0.0227 (11)	0.0139 (12)
C13	0.0545 (11)	0.0482 (13)	0.0485 (11)	0.0039 (9)	0.0168 (9)	0.0007 (10)
C14	0.0387 (9)	0.0631 (14)	0.0350 (9)	−0.0016 (8)	0.0171 (8)	0.0002 (9)
C15	0.0499 (12)	0.0755 (17)	0.0601 (13)	−0.0119 (11)	0.0267 (10)	−0.0143 (12)
C16	0.0541 (14)	0.111 (2)	0.0618 (15)	−0.0289 (14)	0.0275 (12)	−0.0200 (15)
C17	0.0396 (11)	0.135 (3)	0.0495 (13)	−0.0052 (14)	0.0200 (10)	0.0048 (15)
C18	0.0518 (13)	0.104 (2)	0.0636 (15)	0.0196 (14)	0.0278 (11)	0.0205 (15)
C19	0.0481 (11)	0.0691 (16)	0.0570 (13)	0.0066 (10)	0.0243 (10)	0.0072 (11)
N1	0.0382 (8)	0.0505 (12)	0.0492 (10)	−0.0036 (7)	0.0184 (7)	−0.0092 (8)
N2	0.0535 (10)	0.0533 (12)	0.0605 (12)	−0.0005 (8)	0.0294 (9)	−0.0071 (9)
O1	0.0614 (10)	0.0610 (11)	0.0812 (12)	−0.0048 (7)	0.0226 (9)	0.0008 (9)
O2	0.0737 (11)	0.0559 (11)	0.0707 (11)	0.0117 (8)	0.0220 (9)	0.0046 (9)
O3	0.0958 (14)	0.0607 (12)	0.0903 (13)	−0.0195 (10)	0.0329 (11)	−0.0274 (10)

Geometric parameters (Å, º) top

C1—C2	1.510 (3)	C9—N2	1.459 (3)
C1—C7	1.543 (2)	C10—C11	1.367 (4)
C1—C6	1.547 (3)	C10—H10	0.9300
C1—H1	0.9800	C11—C12	1.376 (4)
C2—O1	1.202 (3)	C11—H11	0.9300
C2—C3	1.505 (3)	C12—C13	1.380 (3)
C3—C4	1.521 (4)	C12—H12	0.9300
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C15	1.391 (3)
C4—C5	1.494 (4)	C14—C19	1.392 (3)
C4—H4A	0.9700	C14—N1	1.399 (2)
C4—H4B	0.9700	C15—C16	1.388 (3)
C5—C6	1.523 (3)	C15—H15	0.9300
C5—H5A	0.9700	C16—C17	1.378 (4)
C5—H5B	0.9700	C16—H16	0.9300
C6—H6A	0.9700	C17—C18	1.371 (4)
C6—H6B	0.9700	C17—H17	0.9300
C7—N1	1.448 (3)	C18—C19	1.373 (3)
C7—C8	1.541 (3)	C18—H18	0.9300
C7—H7	0.9800	C19—H19	0.9300
C8—C13	1.387 (3)	N1—H1A	0.85 (2)
C8—C9	1.395 (3)	N2—O2	1.214 (2)
C9—C10	1.398 (3)	N2—O3	1.219 (3)

C2—C1—C7	116.84 (17)	C9—C8—C7	124.96 (18)
C2—C1—C6	108.61 (18)	C8—C9—C10	123.4 (2)
C7—C1—C6	111.16 (16)	C8—C9—N2	121.02 (19)
C2—C1—H1	106.5	C10—C9—N2	115.56 (19)
C7—C1—H1	106.5	C11—C10—C9	119.2 (2)
C6—C1—H1	106.5	C11—C10—H10	120.4
O1—C2—C3	121.7 (2)	C9—C10—H10	120.4
O1—C2—C1	123.57 (18)	C10—C11—C12	119.0 (2)
C3—C2—C1	114.8 (2)	C10—C11—H11	120.5
C2—C3—C4	110.71 (19)	C12—C11—H11	120.5
C2—C3—H3A	109.5	C11—C12—C13	121.0 (2)
C4—C3—H3A	109.5	C11—C12—H12	119.5
C2—C3—H3B	109.5	C13—C12—H12	119.5
C4—C3—H3B	109.5	C12—C13—C8	122.4 (2)
H3A—C3—H3B	108.1	C12—C13—H13	118.8
C5—C4—C3	111.2 (2)	C8—C13—H13	118.8
C5—C4—H4A	109.4	C15—C14—C19	118.60 (19)
C3—C4—H4A	109.4	C15—C14—N1	121.8 (2)
C5—C4—H4B	109.4	C19—C14—N1	119.5 (2)
C3—C4—H4B	109.4	C16—C15—C14	119.8 (2)
H4A—C4—H4B	108.0	C16—C15—H15	120.1
C4—C5—C6	111.1 (2)	C14—C15—H15	120.1
C4—C5—H5A	109.4	C17—C16—C15	120.9 (3)
C6—C5—H5A	109.4	C17—C16—H16	119.6
C4—C5—H5B	109.4	C15—C16—H16	119.6
C6—C5—H5B	109.4	C18—C17—C16	119.3 (2)
H5A—C5—H5B	108.0	C18—C17—H17	120.4
C5—C6—C1	112.4 (2)	C16—C17—H17	120.4
C5—C6—H6A	109.1	C17—C18—C19	120.7 (3)
C1—C6—H6A	109.1	C17—C18—H18	119.6
C5—C6—H6B	109.1	C19—C18—H18	119.6
C1—C6—H6B	109.1	C18—C19—C14	120.7 (2)
H6A—C6—H6B	107.9	C18—C19—H19	119.6
N1—C7—C8	113.92 (16)	C14—C19—H19	119.6
N1—C7—C1	109.45 (16)	C14—N1—C7	121.03 (17)
C8—C7—C1	113.04 (15)	C14—N1—H1A	112.7 (14)
N1—C7—H7	106.6	C7—N1—H1A	114.4 (14)
C8—C7—H7	106.6	O2—N2—O3	122.8 (2)
C1—C7—H7	106.6	O2—N2—C9	118.52 (18)
C13—C8—C9	114.90 (19)	O3—N2—C9	118.7 (2)
C13—C8—C7	120.08 (18)

C7—C1—C2—O1	0.1 (3)	C8—C9—C10—C11	−1.0 (3)
C6—C1—C2—O1	126.8 (2)	N2—C9—C10—C11	179.8 (2)
C7—C1—C2—C3	−179.56 (18)	C9—C10—C11—C12	1.9 (3)
C6—C1—C2—C3	−52.9 (2)	C10—C11—C12—C13	−0.4 (4)
O1—C2—C3—C4	−125.0 (3)	C11—C12—C13—C8	−2.1 (4)
C1—C2—C3—C4	54.7 (3)	C9—C8—C13—C12	2.9 (3)
C2—C3—C4—C5	−55.0 (3)	C7—C8—C13—C12	−179.79 (19)
C3—C4—C5—C6	56.5 (3)	C19—C14—C15—C16	−1.2 (3)
C4—C5—C6—C1	−56.3 (3)	N1—C14—C15—C16	−178.5 (2)
C2—C1—C6—C5	52.8 (3)	C14—C15—C16—C17	0.0 (4)
C7—C1—C6—C5	−177.3 (2)	C15—C16—C17—C18	1.6 (4)
C2—C1—C7—N1	56.4 (2)	C16—C17—C18—C19	−2.0 (4)
C6—C1—C7—N1	−69.0 (2)	C17—C18—C19—C14	0.8 (4)
C2—C1—C7—C8	−71.8 (2)	C15—C14—C19—C18	0.8 (3)
C6—C1—C7—C8	162.83 (19)	N1—C14—C19—C18	178.2 (2)
N1—C7—C8—C13	−32.7 (2)	C15—C14—N1—C7	−39.6 (3)
C1—C7—C8—C13	93.1 (2)	C19—C14—N1—C7	143.1 (2)
N1—C7—C8—C9	144.35 (18)	C8—C7—N1—C14	−63.0 (2)
C1—C7—C8—C9	−89.9 (2)	C1—C7—N1—C14	169.39 (18)
C13—C8—C9—C10	−1.4 (3)	C8—C9—N2—O2	44.2 (3)
C7—C8—C9—C10	−178.57 (17)	C10—C9—N2—O2	−136.5 (2)
C13—C8—C9—N2	177.87 (17)	C8—C9—N2—O3	−137.9 (2)
C7—C8—C9—N2	0.7 (3)	C10—C9—N2—O3	41.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.85 (2)	2.31 (2)	2.906 (3)	127.0 (18)
N1—H1A···O2ⁱ	0.85 (2)	2.48 (2)	3.246 (3)	150.2 (19)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₃
M_r	324.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.0535 (8), 11.9947 (7), 17.2267 (15)
β (°)	117.355 (6)
V (Å³)	1661.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.62 × 0.43 × 0.21

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.784, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	10888, 3434, 2210
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.160, 0.97
No. of reflections	3434
No. of parameters	221
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.23

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2–8), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.85 (2)	2.31 (2)	2.906 (3)	127.0 (18)
N1—H1A···O2ⁱ	0.85 (2)	2.48 (2)	3.246 (3)	150.2 (19)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

The research council of the University of Maragheh is acknowledged for financial support.

References

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